17799-61-0

Basic information

• Product Name: 1H-Pyrrole, 3,4-dimethyl-2,5-diphenyl-
• CAS NO: 17799-61-0
• Molecular Formula: C18H17N
• Molecular Weight: 247.34
• Mol File: 17799-61-0.mol

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole, 3,4-dimethyl-2,5-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 3,4-dimethyl-2,5-diphenyl-(17799-61-0)
• EPA Substance Registry System: 1H-Pyrrole, 3,4-dimethyl-2,5-diphenyl-(17799-61-0)

Safety Data

• Hazardous Substances Data: 17799-61-0(Hazardous Substances Data)

Upstream product

• 34733-55-6 2,3-dimethyl-1,4-diphenyl-butane-1,4-dione 
• 73893-85-3 (2R*,3S*)-2,3-dimethyl-1,4-diphenylbutane-1,4-dione 
• 86971-60-0 (Z)-3-amino-3-phenylacrylic acid methyl ester 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 1426021-96-6 (E)-1-phenylpropan-1-one O-acetyl oxime 
• 61795-22-0 (1-azidoethene-1,2-diyl)dibenzene 
• 952-06-7 deoxybenzoin oxime 
• 451-40-1 phenyl benzyl ketone 
• 16483-98-0 2,3-diphenyl-2H-azirine 
• 13901-70-7 dimethyl 2,5-diphenyl-1H-pyrrole-3,4-dicarboxylate 
• 23517-42-2 propiophenone oxime 
• 503-17-3 dimethylacetylene 
• 34733-55-6 (2R*,3R*)-2,3-dimethyl-1,4-diphenylbutane-1,4-dione 
• 75167-71-4 4,4'-Dimethyl-3,3'-diphenyl-4H,4'H-[4,4']biisoxazolyl-5,5'-dione 

Relevant articles and documents

Synthesis of Polycarbonyl Pyrroles via K2S2O8-Mediated Oxidative Cyclization of Enamines

A novel K2S2O8-promoted oxidative cyclization of enamines is described. A variety of enamines having diverse functional groups and substitution patterns react well using K2S2O8 as the oxidant in the absence of catalyst. This protocol provides a very simple route for the synthesis of polycarbonyl pyrroles and has the advantages of readily available starting materials, mild reaction conditions, and a wide scope of substrates.

Divergent Iron-Catalyzed Coupling of O-Acyloximes with Silyl Enol Ethers

An iron-catalyzed coupling reaction of O-acyloximes and O-benzoyl amidoximes with silyl enol ethers is reported. The protocol provides access to functionalized pyrroles, 1,6-ketonitriles, pyrrolines and imidazolines via carbon-centered radicals generated from an initially formed iminyl radical. The intramolecular cyclization and ring-opening processes of the iminyl radical take place preferentially over reactions that proceed through a 1,3-hydrogen transfer, providing insights into iron-catalyzed reactions with oxime derivatives. The cheap and environmentally friendly iron catalyst, the broad substrate scope and the functional group compatibility make this protocol useful for synthesis of valuable nitrogen-containing products.

Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions

A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful. Photo(chemistry) op: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been established under the irradiation of visible light in the presence of an organic dye. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the formal synthesis of an inhibitor for HMG-CoA reductase.

Copper-catalyzed homocoupling of ketoxime carboxylates for synthesis of symmetrical pyrroles

A novel and efficient copper-catalyzed homocoupling of ketoxime carboxylates has been developed for the synthesis of symmetrical pyrroles. This reaction tolerates a wide range of functional groups and provides a synthetically useful process to synthesize

Synthesis of 2,3,4,5-tetrasubstituted pyrroles from aromatic ketoximes using the TiCl4/Et3N reagent system

Aryl alkyl ketoximes react with the TiCl4/Et3N reagent to give 2,3,4,5-tetrasubstituted pyrroles in moderate to good yields (55-81%).

Intermediates in the Paal-Knorr Synthesis of Pyrroles

The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored.In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m).This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step.The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:0.3:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.

Organische Synthesen mit Uebergangsmetall-Komplexen XLIX. Pyrrole aus einem Aminocarben-Chromkomplex und Alkinen: Synthese eines neuartigen β-Tripyrrans sowie eines cyclischen β-Trispyrrols

A β-tripyrane XI and a cyclic β-trispyrrole XII were obtained by means of a novel two-step pyrrole synthesis from pentacarbonyl(1-amino-1-phenylmethylene)chromium IV via an intermediate iminocarbene complex VI.VI adds alkynes VIIa-e to give the 1H-pyrrole

Organische Synthesen mit Uebergangsmetall-Komplexen XLV. 3-Hydroxypyridine, 1H-Pyrrole und 2-Hydroxypyrrol-Derivate aus einem Aminocarben-Chromkomplex und Alkinen

Pyrroles VI, 3-hydroxypyridines V and 2-hydroxypyrroles IX have been obtained from (amino,phenylcarbene)pentacarbonyl-chromium (I) by simple two-step procedures.The first step involves the generation of 2-azaallenyl(pentacarbonyl)chromium complexes III, and VIII by condensation of I with an aldehyde II and an acid chloride VII, respectively.Complexes III react with alkynes IVa-i to give pyrroles VI and 3-hydroxypyridines V.VIII adds alkynes IVa,e,g to give 2-hydroxypyrroles IX.